From Richmond to Virginia Beach by Bike: How Virginia’s Trail Network Is Coming Together

Aug 19 '26

By John Womeldorf, Mr. Williamsburg

Every home has a story—and increasingly, that story includes what residents can reach without getting into a car.

My partner, Lisa, and I are avid cyclists. We have cycled throughout Virginia and in many other states across the country. We have also explored Ireland, France, Austria, Germany, Hungary, Portugal, the Netherlands and several other countries by bicycle.

Cycling gives you an entirely different perspective on a destination. You move slowly enough to appreciate the landscape, meet people and discover small towns, restaurants and businesses you might otherwise pass by.

When we travel to ride, we especially enjoy staying in short-term rentals along or near the trails. They give us room for our bicycles and gear, allow us to experience the surrounding community and often put us much closer to the places we want to explore.

Those experiences ultimately inspired me to create my own short-term rental along the Virginia Capital Trail in Charles City County. I saw firsthand how many cyclists, walkers and outdoor travelers were looking for comfortable lodging with convenient trail access.

My next project is to build a new cottage next door, giving visitors another short-term rental option near the Capital Trail. I believe trail-oriented tourism will continue to grow as Virginia’s regional bicycle network becomes more connected.

As a Realtor, I am also hearing a new priority from more buyers:

“How close is the house to a bike trail?”

For some people, that means having a safe place for an evening ride or morning walk. For others, it means being able to bicycle from their neighborhood to parks, restaurants, schools or work. Trail access is becoming a genuine quality-of-life consideration—and could become an increasingly important feature for communities from Richmond to Williamsburg, Hampton Roads and Virginia Beach.

The exciting part is that a much larger trail network is beginning to take shape.

The important caveat is that it is not yet possible to ride on one continuous, protected multi-use trail from Richmond to the Virginia Beach Oceanfront. Many pieces already exist, while others remain in planning, design, funding or construction.

Still, the long-term vision is remarkable.

The Backbone We Already Have: The Virginia Capital Trail

The Virginia Capital Trail⁠ is the established backbone of Central Virginia’s trail system.

The fully paved, 51.7-mile multi-use trail stretches from Richmond’s riverfront to Jamestown Settlement in James City County. Along the way, it passes through Richmond, Henrico County, Charles City County and James City County, largely following the historic Route 5 corridor.

It is already one of Virginia’s premier cycling destinations.

The trail offers a little of everything: farmland, wooded stretches, river views, historic sites, bridges, restaurants and access to several parks. Riders can choose a short out-and-back trip or tackle the entire route. Walkers, runners, skaters and families with children also use the trail.

For those of us living in the Williamsburg area, the Jamestown trailhead makes the Capital Trail an especially valuable amenity. Chickahominy Riverfront Park provides another popular access point, with parking, camping and recreational facilities.

Lisa and I ride the Capital Trail regularly, and it is easy to understand why people are drawn to it. You can spend an hour riding beside the James River, make a morning trip to Charles City or devote an entire day to traveling between Jamestown and Richmond.

The Capital Trail is not simply a recreational path. It has become an active-transportation corridor, tourism attraction and economic-development asset connecting communities and businesses along its route.

How the Capital Trail Inspired My Charles City Rental

Our cycling travels have taught us that convenient lodging can make an enormous difference in the trail experience.

When we ride in other states and countries, we frequently choose short-term rentals. We like having a place where we can securely store our bicycles, organize our equipment, prepare meals and relax after a long day of riding.

That experience influenced my decision to create a short-term rental along the Virginia Capital Trail in Charles City County. You can check out my Airbnb on this link

The location gives guests convenient access to the trail while allowing them to experience the quiet, rural character of Charles City. It can serve cyclists traveling between Richmond and Jamestown, visitors exploring the area in shorter sections or travelers who simply want a peaceful place near one of Virginia’s best recreational amenities.

My next project will be constructing a new cottage next door, creating another short-term rental for cyclists and other visitors.

I believe this is a small example of the larger economic impact that trails can have. Once a trail is established, people need places to stay, eat, shop, repair their bicycles and spend time before and after their rides.

The Capital Trail brings visitors into communities they might otherwise drive past. Those visitors support local restaurants, stores, attractions, lodging properties and service businesses.

Bringing the Capital Trail Into Williamsburg

At present, the Virginia Capital Trail ends near Jamestown Settlement rather than continuing directly into Colonial Williamsburg.

That is expected to change.

Through a partnership involving the Tidewater Trails Alliance and Virginia Capital Trail Foundation, plans call for an approximately 7.5-mile official extension running from the vicinity of Jamestown High School to South England Street in Colonial Williamsburg.

The project is expected to represent an investment of approximately $25 million to $33 million. Beyond simply adding mileage, it would create a much more meaningful connection among the existing Capital Trail, Williamsburg neighborhoods, schools, businesses and the Historic Area.

This is especially significant for local residents. A completed extension would make it possible for more people to reach the trail without first loading their bicycles onto a vehicle.

Imagine being able to ride safely from Colonial Williamsburg to Jamestown, continue along the Capital Trail through Charles City and ultimately reach Richmond.

It would also provide a critical western connection for the much larger TRAIL757⁠ vision.

TRAIL757: Connecting Williamsburg and Hampton Roads

TRAIL757 is envisioned as a long-distance multi-use trail system connecting the Peninsula, South Hampton Roads and the Virginia Capital Trail.

The proposed primary TRAIL757 route totals approximately 81.9 miles. When combined with existing and planned regional trails, the broader Hampton Roads trail system could encompass approximately 190 miles.

According to the organization, all 17 Hampton Roads jurisdictions support the vision. Current estimates place the cost of completing the Peninsula portion at approximately $240 million to $300 million, underscoring that this will be a long-term, multi-jurisdictional undertaking rather than a single construction project.

The proposed network would connect or serve communities including:

Williamsburg and James City County
York County and Poquoson
Newport News and Hampton
Fort Monroe
Smithfield, Suffolk and Isle of Wight County
Norfolk, Portsmouth and Chesapeake
Virginia Beach

The goal is not simply to create a recreational ride. TRAIL757 is intended to connect residential neighborhoods with parks, schools, employment centers, healthcare facilities, shopping, tourist attractions and other regional trail systems.

Some portions would use newly constructed shared-use paths, while others would connect existing trails. Exact alignments, funding and construction schedules will differ considerably among jurisdictions.

That is why the TRAIL757 map should be viewed as a long-range vision—not as a route that can be ridden continuously today.

The Peninsula Connection

For Williamsburg-area cyclists, the Peninsula section is particularly important. The proposed network would continue east from Williamsburg through portions of James City County, York County, Newport News and Hampton.

Eventually, riders could have safer connections to destinations such as Newport News Park, the Newport News waterfront and Fort Monroe.

Newport News already has a variety of bicycle facilities and recreational trails, while Hampton has existing routes around Fort Monroe and other parts of the city. The challenge is closing the gaps between them and creating a consistently recognizable, comfortable and protected regional route.

That distinction matters.

A collection of local bicycle lanes and recreational paths does not automatically create a trail that most families would feel comfortable riding from one city to another. Connections, road crossings, signage and separation from high-speed traffic are every bit as important as total mileage.

TRAIL757 is intended to provide that regional framework.

South Hampton Roads and the Elizabeth River Trail

On the south side of Hampton Roads, one of the best-established pieces is Norfolk’s Elizabeth River Trail⁠.

The 10.5-mile urban trail follows Norfolk’s waterfront through 11 sections, connecting 28 neighborhoods as well as parks, universities, historic areas, restaurants, businesses and cultural attractions.

Its route includes destinations such as Harbor Park, Downtown Norfolk, the Freemason Historic District, Fort Norfolk, Chelsea, West Ghent, Old Dominion University, Larchmont and Lochhaven.

The Elizabeth River Trail is a good example of what an urban trail can become. It is not merely pavement running through a city. It links neighborhoods, creates gathering places and provides access to destinations people actually want and need to reach.

Plans call for the Elizabeth River Trail to become part of the approximately 41-mile South Hampton Roads Trail, a future regional corridor through Suffolk, Portsmouth, Chesapeake and Norfolk to Virginia Beach.

Again, portions of this larger corridor exist, but the complete, seamless route does not.

The Virginia Beach Trail

At the eastern end of the regional vision is the planned Virginia Beach Trail⁠.

The completed trail is planned as an approximately 12-mile, 14-foot-wide paved shared-use path extending from the Norfolk border at Newtown Road through Town Center and ultimately to the Oceanfront.

Approximately 1.5 miles already exist along Norfolk Avenue between Birdneck Road and Pacific Avenue near the Resort Area.

Major additional phases are moving forward:

Phase 1 is planned as a 3.2-mile connection between Newtown Road and Constitution Drive near Town Center.
Phase 4 received a $23.8 million SMART SCALE grant for a 2.8-mile section between South Birdneck Road and London Bridge Road.
Design for Phase 4 is tentatively expected to begin in fiscal year 2027, with construction currently anticipated in fiscal years 2031–2032.
Funding is still needed for other portions of the corridor.

When complete, the Virginia Beach Trail would serve as the easternmost segment of the South Hampton Roads Trail and a critical link in the larger Richmond-to-Oceanfront vision.

Virginia Beach already reports more than 300 miles of bikeways and trails, but the planned cross-city trail would provide something different: a recognizable east-west spine capable of joining multiple local facilities into a useful regional network.

The Fall Line Trail: Expanding North and South of Richmond

Richmond will eventually become more than the western endpoint of a Richmond-to-Virginia Beach trail network.

It will also be the intersection of two major regional trail corridors.

The east-west Virginia Capital Trail will connect with the developing Fall Line Trail⁠, a planned 43-mile north-south multi-use trail running from Ashland through Hanover, Henrico and Richmond before continuing through Chesterfield and Colonial Heights to Petersburg.

The Fall Line Trail passes through seven jurisdictions, with more than 20 miles reported as open or under construction. The current target for completing the full corridor is 2034, although individual segments have different funding and construction schedules.

Within Richmond, approximately 13 miles of the route are planned. Some segments are fully funded or moving toward construction, while others are still seeking funding.

One of the most closely watched areas has been Bryan Park. Earlier routing raised concerns about mature trees. Richmond’s planning and design teams subsequently revised the alignment, working with arborists and community representatives to reduce the impact.

The city reports that the current plan calls for six trees to be removed. The alignment enters the critical root zones of 44 of the 328 inventoried trees, with specialized construction and preservation practices planned to minimize damage.

Richmond has published its Fall Line Trail plans, economic-impact analysis and tree-preservation information⁠ for public review.

Once completed, the Fall Line Trail would allow someone to travel north or south through the Richmond region and connect with the Capital Trail heading east toward Williamsburg.

That creates the possibility of a future trail network stretching from Ashland and Petersburg through Richmond, Williamsburg and Hampton Roads to the Atlantic Ocean.

Why Trail Access Matters to Homebuyers

People rarely choose a home based on square footage alone.

They are choosing a lifestyle: where they will walk, exercise, meet neighbors, spend weekends and raise their families. For many buyers, trail access now belongs in the same conversation as schools, commute times, shopping and neighborhood amenities.

I am increasingly working with buyers who ask about:

Homes within riding or walking distance of a trail
Neighborhoods connected to parks and greenways
Safe routes for children and families
Garages or storage areas suitable for bicycles
Access to cycling without traveling on busy roads
The ability to walk or bike to restaurants and community destinations

A trail shown on a future planning map should never be represented as a completed amenity. Buyers need to understand whether a nearby route is open, funded, under design or simply proposed.

But when a high-quality trail is already accessible, it can meaningfully influence how people perceive a neighborhood.

Trail proximity may not matter to every buyer, but for people who value an active lifestyle, it can be a major selling point.

Trails as Economic Development

My experience creating a short-term rental near the Virginia Capital Trail has made the economic potential of trail tourism very real to me.

Cyclists traveling a longer route need more than pavement. They need lodging, food, water, bicycle repairs, transportation and places to stop along the way.

Successful multi-use trails can help:

Strengthen tourism
Support nearby restaurants and small businesses
Increase demand for short-term lodging
Encourage investment around trailheads
Attract and retain employers and workers
Improve access to jobs and services
Enhance the appeal of nearby neighborhoods
Create new community gathering places

The Capital Trail already demonstrates this effect. Businesses along Route 5 and around trail access points benefit from cyclists, runners and visitors who might otherwise pass through the region without stopping.

A more connected trail system could encourage longer trips, overnight stays and multi-day cycling vacations between Richmond, Charles City, Williamsburg and Hampton Roads.

We have experienced this type of trail tourism in the United States and Europe. When a route is safe, well-marked and supported by lodging, restaurants and local businesses, cyclists will plan entire vacations around it.

Virginia has the scenery, history and destinations to attract those travelers.

Health, Transportation and Community Access

Not every trail user is training for a long ride.

Many people simply want a safe place to walk for 30 minutes, take their children for a bicycle ride or travel to work without sharing a high-speed road with automobiles.

Well-designed multi-use trails provide free or relatively low-cost opportunities for exercise. They can improve access for residents who do not own cars and give older adults, families and people with disabilities additional ways to reach community destinations.

Trails also connect people who might otherwise never meet. They pass through neighborhoods, parks, downtown districts and rural landscapes, creating shared public spaces across jurisdictional and economic boundaries.

A Generational Opportunity

Completing the full network will require years of funding, design, property acquisition, environmental review and construction. Some sections will open long before others, and difficult gaps—particularly major water crossings and heavily developed corridors—will require creative solutions.

But Virginia has already proved that ambitious trail projects can become reality.

The Virginia Capital Trail began as a vision. Today, it is a 51.7-mile regional asset enjoyed by residents and visitors from around the world.

TRAIL757, the Williamsburg extension, the South Hampton Roads Trail, the Virginia Beach Trail and the Fall Line Trail represent the next chapter.

The idea that a future cyclist could leave Petersburg or Ashland, ride through Richmond, continue through Charles City to Williamsburg and eventually reach the Virginia Beach Oceanfront on a connected regional network is extraordinary.

As a cyclist, I am excited about the places these trails could take us.

As a short-term rental owner, I see the potential for cycling tourism to support local businesses and communities.

As a Realtor, I believe these trails will increasingly influence where people choose to live, invest and build their lives.

The trail network is incomplete, but the vision is no longer difficult to imagine. Piece by piece—and community by community—it is beginning to take shape.

Learn More

About the Author

John Womeldorf, known throughout the region as Mr. Williamsburg, is a full-time Virginia Realtor with Liz Moore & Associates. For more than 25 years, John has helped buyers and sellers throughout Williamsburg, James City County, York County, Hampton Roads, Richmond and surrounding areas.

John and his partner, Lisa, are avid cyclists. They have ridden extensively throughout Virginia and in many other states, as well as in Ireland, France, Austria, Germany, Hungary, Portugal, the Netherlands and other countries.

Their cycling travels—and their preference for staying in short-term rentals near the trails they ride—inspired John to create his own short-term rental along the Virginia Capital Trail in Charles City County. His next project is building a new cottage next door to provide another lodging option for cyclists and visitors.

If living near a trail, park or other outdoor amenity is part of your next-home wish list, John would be happy to help you explore the communities offering the lifestyle you are seeking.

John Womeldorf | Mr. Williamsburg
Liz Moore & Associates
Call or text: 757-254-8136
Email: John@MrWilliamsburg.com⁠
Website: MrWilliamsburg.com⁠
Licensed in the Commonwealth of Virginia

Office locations: Williamsburg, Oyster Point/Newport News, Richmond/Short Pump, Kilmarnock, Virginia Beach, Northern Neck and the Peninsula.